Benzoate dioxygenase from Ralstonia eutropha B9 – unusual regiochemistry of dihydroxylation permits rapid access to novel chirons

Abstract

Oxidation of benzoic acid by a microorganism expressing benzoate dioxygenase leads to the formation of an unusual ipso, ortho arene cis-diol in sufficient quantities to be useful for synthesis. This homochiral diol possesses an array of differentiated functionality which can be exploited to access diverse highly oxygenated structures by concise synthetic sequences.